You don't really take it in at the time, but there's a clue at the start of Initiation Love that alerts you to the dual nature of the film. It seems like just a nostalgic reference to the film's 1980s' setting but the image of a cassette tape makes the point that it has an A-Side and a B-Side, and there are definitely two sides to Initiation Love.
Side A plays out like a typical romantic comedy of innocent geek love. In Shizuoka city in 1987, overweight and socially awkward Tatsuya Suzuki can't believe his luck when an attractive young woman shows an interest in him. He had only been invited to a group dinner date to make up the numbers, but somehow he immediately makes a connection with Mayuko Naruoka, a beautiful young woman who is clearly way out of his league. Soon however not only are Mayoko and 'Takkun' a regular Friday night item, but Mayoko manages to inspire him to lose weight and transform his whole image.
The transformation is abrupt - involving an entirely different actor - but the changes and the affect it has on the couple's relationship is more gradual as the film flips over to the B-side. Suzuki is transferred to his work's head office in Tokyo and for a while he makes the long commute back to Shizuoka to be with Mayoko at the weekends, but can their long-distance relationship survive? When Miyako, a colleague in the Tokyo office starts to show a romantic interest in him, Suzuki finds himself almost literally torn between the two women.
The dual nature of Initiation Love is important then, and director Yukihiko Tsutsumi (20th Century Boys) is clever in how he lets the innocent bright and colourful lightness of the 80s' romance in the first part of the film develop into something unexpectedly darker in tone. The contrast highlights the division between youthful innocence and the complications of adult life, the difference between life in the provinces and the city, but the passing of time is also a divisive factor, where the nostalgic view we hold of the past and dreams for the future don't always match up with the reality. As the film's opening and potentially confusing twist conclusion highlights, we can't imagine the unexpected and unplanned for changes we go through in life. A cassette doesn't just have an A-Side and a B-Side, but it can be a mixtape as well.